Robert Dell, 62, who stepped down as latham & Watkins’ chairman in January, could have played it safe two decades ago when, at age 43, he was elected the firm’s youngest leader.

Latham had just undergone unprecedented turbulence sparked by the 1990 collapse of its biggest investment banking client, Drexel Burnham Lambert. His predecessor, Jack Walker, had responded by cutting scores of associates and moving to a more reward-driven compensation system.